5 Tips for Being Happily Single on Valentine’s Day

Jessica Massa graduated magna cum laude from Harvard with a degree in psychology. Her work has been featured in The New York Times, The Wall Street Journal, Elle, Variety, CNN.com, The Times of London, and Glamour.com, among others. She lives in Brooklyn.

In middle school, some friends and I protested the holiday by wearing dark clothes and black lipstick and carrying around bouquets of dead roses (of course, I threw those roses in the trash as soon as a sweet guy friend bought me a blooming red one). Years later, I strapped on my stilettos and gathered a group of other single ladies to drink wine, bond over Sex and the City, and toast to the fabulous life of the independent woman. Fast forward to 2010, and a gal pal and I found ourselves crammed into an overcrowded movie theater, ready for our hearts to be warmed by even the most clichéd of love stories as we settled in to watch…Valentine’s Day.

But there was a problem with our attempts to celebrate a day that is—by definition—not for single people. Instead of feeling empowered by our efforts to fight, reclaim, or romanticize Valentine’s Day, these single women and I went home at the end of the night feeling kind of lonely and depressed.

The Gaggle

What are all the single ladies to do? Here’s the good news: You don’t have to overplan, underplan, glorify, or ignore Valentine’s Day just because you don’t have a significant other, or even a date. You can actually enjoy the holiday! Or at the very least, you can refuse to let it turn you into a bitter and lonely hater of all things red and fragrant.

5 DON’Ts for Valentine’s Day
1) DON’T “celebrate” your singlehood with other single women.
You might assume that surrounding yourself with women who are in the same unattached boat is the perfect way to combat the feelings of loneliness that can arise during a day that is built around coupledom. But when a bunch of single women get together because they are single, to remind themselves of why it’s OK to be single, they tend to end up feeling really… single.

A good rule of thumb is this: If you’d be embarrassed to tell your cute male co-worker what you did on Valentine’s Day (“We ate tapas and burned photos of our exes and hit the club to dance in a circle all night long!”), then you probably shouldn’t do it.

2) DON’T force yourself to attend a singles mixer, speed-dating event, or blind date with your grandmother’s dentist’s son.
Being single is not a problem that you have to “fix”—and the day that you are feeling the most pressure to have a romantic partner is not the day to start desperately throwing yourself on the market.

In today’s post-dating world (check out what I mean by that here!), people are increasingly connecting through casual and ambiguous settings where they can be themselves. So skip the formal outings and throw a co-ed dinner party, go to a concert, or volunteer with a local organization.

Be social on Valentine’s Day! Do something that involves members of the opposite sex. But choose an activity that will be fun on its own, whether you end up meeting the love of your life or not. You don’t want to risk going home disappointed. Not on Valentine’s Day.

3) DON’T expect this to be the day when “that guy you’ve been sort of hanging out with” will declare his romantic feelings for you.
Men often feel unwelcome pressure around Valentine’s Day, too. While guys in relationships are stressing over their obligation to plan The Best Evening Ever, single guys are wondering how to handle their more ambiguous relationships.

In this era of romantic “gray areas,” you probably have at least one guy in your life who you think you might have (mutual? who knows!) feelings for. But here’s a hint: he’s probably going to stay silent on Valentine’s Day. His lack of a big romantic gesture—or even a perfunctory text message—doesn’t mean that he’s not into you. It just means that he knows you will read more seriousness into his words and actions on Valentine’s Day than you would on any other day of the year. And given all that pressure, he’d rather keep the lid on that can of worms.

Save yourself the worry of waiting to hear from him, and push him out of your mind for a day. You can comment on his Facebook status and resume your ambiguous flirtation tomorrow.

4) DON’T assume that everyone who has a date is having a better time than you are.
Several Valentine’s Days ago, a girlfriend and I took each other out to a fun sushi restaurant for dinner. The hostess seated us next to a couple, and thus we prepared ourselves for the PDA-filled lovefest that was surely about to be thrown in our faces.

But to our surprise, the couple said 12 words to each other throughout the entire meal, choosing instead to stare glumly at their dragon rolls and scroll through their phones. All while my friend and I had a blast chatting, laughing, and enjoying the good food.

There are definitely couples out there who will have a great time together on Valentine’s Day. But those are probably the same couples who are also having a great time together on Feb. 13, 15, and beyond. So don’t psych yourself out by comparing your plans to everyone else’s. You aren’t a Valentine’s Day failure! In fact, you might even be having more fun than most other people…

5) DON’T get hung up on being “single.” You’re not!
Valentine’s Day can tempt you to categorize your love life into one of two black-and-white boxes: either you’re in a relationship, or you’re not. If you’re in a relationship, then you’re happy and in love. And if you’re single, then you’re desperate and lonely.

Luckily, in today’s shifting romantic landscape, these are no longer your only options.

Why are you not “single?” Because your love life is likely much more vibrant than you realize. In this post-dating world, every interaction with a guy counts—every Gchat conversation with a soccer teammate, every brainstorming session with a colleague, and every catch-up dinner with an old friend. Love can emerge, at any moment, from any of these interactions.

Stop thinking of yourself as a “single” girl. The opportunity to find love is much closer than you think! So feel free to steal some of that festive chocolate for yourself—love might be just around the corner, and isn’t that something worth celebrating?